Although Jack was but twenty-three years of age, he had tasted the bitter cup of Slavery pretty thoroughly under Kendall B. Herring, who was a member of the Methodist Church, and in Jack's opinion a "mere pretender, and a man of a very bad disposition." Jack thought that he had worked full long enough for this Herring for nothing. When a boy twelve years of age, his mother was sold South; from that day, until the hour that he fled he had not heard a word from her. In making up his mind to leave Slavery, the outrage inflicted upon his mother only tended to increase his resolution.
In speaking of his mistress, he said that "she was a right fine woman." Notwithstanding all his sufferings in the Kendall family, he seemed willing to do justice to his master and mistress individually. He left one sister free and one brother in the hands of Herring. Jack was described as a man of dark color, stout, and well-made.